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Potassium Carbonate → 2-dimethylamino-6-(4-ethoxy-3-trifluoromethyl-phenyl)-1H-imidazo[4,5-c]pyridine-4-carbonitrile

HRID 2246436
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HRID 2246436 반응식
Cl[C:2]1[N:7]=[C:6]([C:8]#[N:9])[C:5]2[N:10]=[C:11]([N:13]([CH3:15])[CH3:14])[NH:12][C:4]=2[CH:3]=1.[CH2:16]([O:18][C:19]1[CH:24]=[CH:23][C:22](B(O)O)=[CH:21][C:20]=1[C:28]([F:31])([F:30])[F:29])[CH3:17].C(=O)([O-])[O-].[K+].[K+]>C1COCC1>[CH3:14][N:13]([CH3:15])[C:11]1[NH:12][C:4]2[CH:3]=[C:2]([C:22]3[CH:23]=[CH:24][C:19]([O:18][CH2:16][CH3:17])=[C:20]([C:28]([F:29])([F:31])[F:30])[CH:21]=3)[N:7]=[C:6]([C:8]#[N:9])[C:5]=2[N:10]=1
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참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 445581844-Ethoxy-3-(trifluoromethyl)benzeneboronic acidHCID 589381326-chloro-2-dimethylamino-1H-imidazo[4,5-c]pyridine-4-carbonitrile

생성물 1

HCID 589381232-dimethylamino-6-(4-ethoxy-3-trifluoromethyl-phenyl)-1H-imidazo[4,5-c]pyridine-4-carbonitrile수율 3%

시약·촉매·용매 1

HCID 8028
Tetrahydrofuran
용매

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온도
130 °C

실험 절차

A suspension of 6-chloro-2-dimethylamino-1H-imidazo[4,5-c]pyridine-4-carbonitrile (100 mg, 0.45 mmol), 4-ethoxy-3-trifluoromethyl-phenyl boronic acid (198 mg, 0.88 mmol) tetrakis(triphenylphosphine)palladium(0) (50 mg, ˜10 mol %) and potassium carbonate (193.0 mg, 1.39 mmol) in THF (3 ml) was heated to 130° C. for 6 minutes in the “Smith” microwave. The crude mixture was concentrated under reduced pressure to remove THF before partitioning between ethyl acetate and water. The organic layer was separated, dried over sodium sulfate and concentrated under reduced pressure. The material was then dissolved in DMSO and purified in aliquots by preparative HPLC. The desired fractions were collected and concentrated to give a white solid which was washed with ether to afford 2-dimethylamino-6-(4-ethoxy-3-trifluoromethyl-phenyl)-1H-imidazo[4,5-c]pyridine-4-carbonitrile (5.0 mg)

후처리

  1. concentrationThe crude mixture was concentrated under reduced pressure
  2. customto remove THF
  3. custombefore partitioning between ethyl acetate and water
  4. customThe organic layer was separated
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. dissolutionThe material was then dissolved in DMSO
  8. custompurified in aliquots by preparative HPLC
  9. customThe desired fractions were collected
  10. concentrationconcentrated
  11. customto give a white solid which
  12. washwas washed with ether

출처 및 근거

ORD 기록
ord-102f7f63ac584b16ad4ba8611f9f5416
출처 데이터셋
uspto-grants-2010_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07687515B2

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